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Custom Vacations to Italy
Crafted for Your Family
With more destinations, accommodations & things to do, your family will experience Italy like a local, not a tourist.
Tell us your preferences and ideal locations Takes 3 minutes to complete!
Every single detail
Planned to perfection
Each custom itinerary includes flights, accommodations, dining, activities and more
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Custom
Itineraries
Explore Italy your way with bespoke travel itineraries
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First-class
Accommodations
Exceptional lodging options for you to unwind & relax
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Authentic
Food & Wine
Indulge in the finest regional cuisine & superb wines
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Local
Guided Tours
Intimately explore Italy's most renowned & iconic sites
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Effortless
Connections
Seamlessly coordinated flights to & travel within Italy
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Flexible
Planning
Effortlessly modify and customize your travel itinerary
A completely fresh take on
Traveling to Italy
Experience Italy like a local with our personalized travel plans tailored just for you.
- A vacation to Italydesigned exclusively for you
- Every detail of your trip, including the cities, food, tours, and nightlife, will be crafted to your exact preferences
- Helping you discover thehidden wonders of Italy
- We want you to see Italy from a local's perspective. Our native team will help you avoid tourist traps and uncover the authentic Italy.
- By the team that does travel to ItalyAnd nothing else
- You deserve a unique, one-of-a-kind honeymoon experience from a company focused exclusively on Italian travel - not a pre-built "package".
Your next Italy vacation
Easy as 1, 2, 3
You're in control
1. Describe your ideal trip
Activities you enjoy, and the cities and regions on your must-visit list Prefer the beach, the city, or the country-side? Maybe all of the above? When will you depart, and how long do you want to stay?
We collaborate
2. Together, we fine-tune the details
Activities you enjoy, and the cities and regions on your must-visit list Prefer the beach, the city, or the country-side? Maybe all of the above? When will you depart, and how long do you want to stay?
Your dream becomes reality
3. You receive your custom itinerary
Activities you enjoy, and the cities and regions on your must-visit list Prefer the beach, the city, or the country-side? Maybe all of the above? When will you depart, and how long do you want to stay?
Family Activities in Rome
A family trip to Rome, the 'Eternal City', presents a remarkable blend of historical marvels and engaging activities for all ages. Begin your adventure at the iconic Colosseum, where you can step back into ancient times and imagine the thrilling gladiator battles that once took place. For a hands-on experience, enroll the family in a Roman Gladiator School where you can learn about ancient Roman history and even train in gladiator combat techniques. In Vatican City, make sure to visit the awe-inspiring St Peter's Basilica, an architectural masterpiece that holds centuries of religious significance. The combination of ancient history, timeless architecture, and engaging experiences makes Rome an exceptional destination for a family trip filled with education, adventure, and unforgettable memories.
Family Activities in Florence
Embark on a captivating family trip to Florence, where a wealth of activities awaits. Explore iconic landmarks like the Duomo and Ponte Vecchio, immersing yourselves in the city's rich history. Unleash your creativity in interactive art workshops and indulge in delightful food tours, savoring authentic Tuscan cuisine. Discover artistic treasures in renowned museums such as the Uffizi and Accademia, including Michelangelo's David. Whether strolling through charming streets or enjoying the beauty of Boboli Gardens, Florence offers an unforgettable family adventure filled with history, art, and culinary delights.
Family Activities in Venice
Experience the magic of a family vacation in Venice. Glide along picturesque canals on a gondola, taking in the iconic sights of Rialto Bridge and St. Mark's Square. Immerse yourselves in the rich history at Doge's Palace and Basilica di San Marco. Wander through charming streets, uncovering hidden gems, and indulge in the flavors of Venetian cuisine. Embrace the vibrant culture with a mask-making workshop, capturing the essence of Venice's Carnival tradition. Explore nearby Murano for its glass-blowing heritage and Burano for its colorful houses. Venice promises an enchanting family adventure, creating cherished memories that will last a lifetime.
More couples honeymoon with
Trips 2 Italy
One of a Kind
Family Vacations to Italy
Just as every family is wonderfully unique, so should be their holidays, and that's what we aspire to achieve at Trips 2 Italy. We are dedicated to curating personalized Italy family vacation packages that are as distinctive as your family's dynamic. While standard vacation packages may offer some enjoyable experiences, they fall short of the truly bespoke experiences that a custom Italy family vacation can provide. In planning a custom trip with us, we pay attention to every detail, ensuring that each itinerary is meticulously tailored to match the diverse interests, needs, and dreams of each family member. Embrace the joy of discovering Italy's cultural riches, culinary delights, and scenic beauty, all at a pace that suits your family, creating unforgettable memories to be cherished for a lifetime.
Crafted by a Team
That Specializes in Italian travel
Trips 2 Italy is fueled by a team of dedicated Italian-born travel experts, all led by our founder, Tommaso. Our intimate, firsthand knowledge of our homeland enables us to offer you exceptional recommendations for hotels, must-visit places, engaging activities, and remarkable sights. We don't just suggest; we personally select and book flights, provide transportation throughout your stay, and manage every detail in between. This hands-off approach is designed to ensure that every moment of your journey is enjoyed without the hassle of logistics. Our commitment is to offer you an Italian experience that reflects our love for the country, while ensuring your trip is as seamless and memorable as possible.
Book your Family Vacation
With Complete Peace of Mind
Exclusively from Trips 2 Italy, we offer our new flexible travel plan, tailored to provide peace of mind for our family travelers. This plan allows you to reschedule your family vacation up to 30 days before your scheduled departure date without incurring any fees or costs. We understand that plans can change, especially when traveling with family, and we want to ensure your experience is stress-free. If changes occur to your itinerary or the international travel situation after your family trip is booked, we will promptly contact you to discuss any alterations and your options, which can include modifying or postponing your trip. Should you decide to delay your journey, Trips 2 Italy will issue a letter of credit, ensuring 100% of your payment towards the booking is preserved. This way, you and your family can look forward to exploring the beauty of Italy, knowing you're in flexible and caring hands.
Curious what our honeymoons are like?
Explore this itinerary
- Day 1
Rome
Your family adventure begins
As you step out of the airport, take a deep breath and let the magic of Italy snare your senses. After a ride to your lodging for the next few days, opt to unpack later and instead take advantage of the daylight and explore the city. A few landmarks of Rome you will not want to miss include the Borghese Gallery which is home to an extensive private collection of art from various time periods, the Basilica di Santa Maria Maggiore for gorgeous frescoes and mosaics, and the Piazza del Popolo for a taste of local culture. Spend the evening however you like, but begin it with dinner at a cozy Italian restaurant for an amazing local dinner.
- Day 2
Rome
Lose yourself in the piazzas
Rome is a large city filled with historic and architectural treasures that cannot be seen in the space of one day, much less three. So today, explore the city at your leisure making sure to stop at the Fontana di Trevi, or Trevi Fountain, to witness one of the most beautiful fountains in Europe that features a number of stunning statues that give the fountain a regal touch. Next wander through Piazza Navona, a famous public square featured in many films including Dan Brown’s Angels & Demons which is fabulous for people watching. If time allows, be sure to visit the famous Spanish Steps adjacent to the Piazza di Spagna and take in the sunset at the majestic Vitoriano.
- Day 3
Rome
Explore St. Peter’s Basilica
Breakout your best clothes for today as you and your love will be visiting the Vatican. This religious complex sometimes referred to as one of the world’s smallest countries, is packed with internationally recognized art and history inside the walls of St. Peter’s Basilica, on St. Peter’s Square, and in the Vatican museums and Sistine Chapel. A visit to the Vatican is said by religious and non-religious visitors alike to be a very moving experience. If you are visiting on a Wednesday when the Pope is in Rome, you may even be able to attend a Papal Audience at the Vatican. Traditionally the Pope appears to visitors and gives a Papal Blessing. This will certainly be a very special memory.
- Day 4
Rome
Trace the steps of gladiators at the colosseum
Today you will be visiting one of the most iconic symbols of Rome, the Roman Colosseum. This dramatic structure traces centuries back to the early Roman period. These ruins are still intact enough that to stand in the middle of the arena and picture a crowd going wild as a gladiator and his opponent step into the ring to battle for survival feels eerily realistic. A guided tour will also provide a visit to the underground Colosseum where you can virtually trace the steps of gladiators as they waited for their turn in the spotlight.
- Day 5
Rome
Hold your family tight in the catacombs
For a truly unique view of Rome, visit the catacombs or underground burial sites that date as far back as the second century. Although only a handful are open to the public, an estimated sixty or more catacombs can be found in Rome and stretch hundreds of kilometers. Traveling these subterranean passageways is an adventure unlike any you’ve experienced here so far. Some of the more popular catacombs you may want to visit include San Sebastiano, Domitilla, Priscilla, and Sant’Agnese. This activity is both exciting and fascinating and gives you an excuse to hold on extra tight to your love.
- Day 6
Assisi
Enjoy a sunset dinner in rolling hills of Umbria
Your time in Rome has now drawn to a close, so say Addio to the city and look forward to your journey to Assisi. This picturesque town who is said to have been the hometown of St. Francis, sits atop the rolling hills of Umbria and is a United Nations Educational Scientific Cultural Organization (UNESCO) World Heritage Site. Once you have arrived in Assisi and have had time to deposit your luggage at your new place of lodging, consider a stroll through this ancient town’s historic city center. As darkness begins to blanket the city, find a lovely restaurant for dinner and toast to a new adventure in Assisi.
- Day 7
Assisi
Embark to medieval fortress from the 14th century
After a leisurely breakfast, set out to explore the medieval fortress of Rocca Maggiore and some of the local churches. Rocca Maggiore is a fourteenth century castle that stands tall at the very highest part of the city and offers stunning views of Assisi, Perugia and beyond. The area is also home to a number of historical churches that are worth a visit including the famous Basilica of St. Francis, Santa Maria Sopra Minerva, Santa Maria degli Angeli, Duomo di San Rufino, Chiesa Nuova, San Damiano, and the Basilica di Santa Chiara.
- Day 8
Florence
Be swept up by the charm of Florence
This morning you will leave Assisi behind and travel to the gorgeous city of Florence. This beautiful but large town in the heart of Tuscany is full of amazing architecture, art, and cuisine. Once you have checked in to your new living quarters, take a little time to tour some of the main sights of Florence including Florence Duomo, Ponte Vecchio, and Piazza della Signoria. End your day with an evening cooking class that is sure to reveal the secrets of fine Italian cuisine and finish with a spectacular glass of wine.
- Day 9
Florence
Marvel in great food and art
You may want to eat light if at all this morning for breakfast because first on the agenda for today is a food tour through some of Florence’s most charming neighborhoods. You and your family will indulge in authentic Italian appetizers, first and second courses, and even desserts. After all that food, a lengthy walk through the Accademia Gallery is in order. Here you will behold famous masterpieces by renowned artists including David which was sculpted by Michelangelo.
- Day 10
Florence
Tour San Gimignano finest winery
Today you will be leaving the busiest part of Florence for a day excursion to San Gimignano, a medieval town well known for being a UNESCO World Heritage Site and its production of Vernaccia di San Gimignano wine. For lunch, visit a Chianti winery and do the hard work of taste-testing some of the finest Tuscan wines over a light but delicious Italian lunch. Then head to another medieval town, Siena, to take in the fabulous architecture and visit the site of the famous Piazza Il Campo horse race.
- Day 11
Florence
Learn to cook, as a family
After a leisurely breakfast and morning, attend an Italian cooking class. Here you will learn about the importance of fresh and quality ingredients in creating mouthwatering homemade meals. Once you’ve covered the basics, you and your family will go with the class to tour a Florence market to learn how to identify the best picks for assembling your meal. Learning how to cook here is a fantastic way to bring a little bit of Florence home with your loved ones.
- Day 12
Venice
Unwind then explore the magic of Venice
Alas, this morning you will conclude your time in Florence to leave for your final destination of Venice. Sometimes called the floating city, Venice is actually a series of islands separated by waterways and connected by bridges. Upon your arrival, simply take the day to explore the islands at leisure and stroll through this romantic and magical city hand in hand.
- Day 13
Venice
An old-world gondola ride awaits
Start your day with a visit to the beautiful St. Mark’s Basilica, one of the most visited churches in Venice. The church is sometimes nicknamed the Church of Gold because of the Byzantine glass mosaics that cover much of the inside and outside. After you’ve overcome the pleasant surprise of roughly eighty-five thousand square feet of mosaics inside the church, it is time for one of the most time-honored traditions of Venice, a gondola ride. Sail through the canals of the city with your gondola operator providing a brief history of important landmarks.
- Day 14
Venice
Voyage to the Venetian islands
Today is a day of choices between an excursion to the Venetian islands of Murano, Burano, and Torcello or an excursion to nearby Verona. A trip to Murano, Burano, and Torcello will yield glassblowing and lace-making demonstrations that make fabulous trip souvenirs that'll become family heirlooms. The most popular highlight for an excursion to Verona is visiting the setting of Shakespeare’s renowned literary work, Romeo and Juliet. Immerse yourselves in the star-crossed lovers’ story by touring Romeo’s house as well as Juliet’s house and tomb.
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